HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-(Pyridin-3-yl)but-3-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Bromopyridine | HCID 12286 | — |
| Reactant | 3-Butyn-1-OL | HCID 13566 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(Pyridin-3-yl)but-3-yn-1-ol | HCID 10582917 | 12.3% |
Reaction Steps
To a stirred solution of 3-bromopyridine (3.75 g, 23.8 mmol), 3-butyn-1-ol (2.0 g, 28.5 mmol) and triethylamine (12 ml) in anhydrous DCM was added bis(triphenylphosphine)palladium dichloride (0.05 g, 0.07 mmol) and copper(I) iodide (0.05 g, 0.26 mmol). The mixture was refluxed for 20 h under argon. After cooling, water (20 ml) was added and the product extracted into DCM. The combined organics were dried over anhydrous potassium carbonate, filtered and evaporated to give a brown oil. Column chromatography (flash silica gel, ethyl acetate) gave 4-(3-pyridyl)-1-but-3-ynol (0.43 g, 12%) as a colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05428168 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-916c019ae2404726a039426cd3dd02e7 |
| Source note | uspto-grants-1995_06 |